4-Mesylphenylacetic acid → 2-[4-(Methylsulfonyl)phenyl]-1-ethanol
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12](O)=[O:13])=[CH:7][CH:6]=1)(=[O:4])=[O:3]>O1CCCC1>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][OH:13])=[CH:7][CH:6]=1)(=[O:3])=[O:4]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
10 g (47 mmole) 4-(methylsulfonyl)phenyl acetic acid was dissolved in 40 ml tetrahydrofuran and the solution was cooled to −10° C. At this temperature 4-(methylsulfonyl)phenyl acetic acid precipitates. 47 ml 1 M borane-tetrahydrofuran complex was added slowly. The reaction mixture was allowed to reach room temperature and the reaction was followed by TLC. After completion 100 ml methanol was added and the solvents were evaporated. The residue was dissolved in dichloromethane and washed with sodium hydroxide. The organic phase was dried, filtered and evaporated in vacuo to give 7.5 g (yield 79.7%) of 2-[4-(methylsulfonyl)phenyl]-1-ethanol.
Workup
- customAt this temperature 4-(methylsulfonyl)phenyl acetic acid precipitates
- addition47 ml 1 M borane-tetrahydrofuran complex was added slowly
- customto reach room temperature
- additionAfter completion 100 ml methanol was added
- customthe solvents were evaporated
- dissolutionThe residue was dissolved in dichloromethane
- washwashed with sodium hydroxide
- customThe organic phase was dried
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-0d1bcb9025e34582be8c503c99af9c21
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06288096B1
Reaction notes
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